Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2025 May 14;23(19):4616-4621.
doi: 10.1039/d4ob01815j.

Chemodivergent synthesis of cis-4-hydroxyprolines from diastereomerically enriched epoxides

Clement DaSilva  1 , Grace Mauk  1 , Lucas Forshee  1 , Oliver Pope  1 , Mathilde Doherty  1 , Max Ongbongan  1 , Nicholas Lutz  1 , Zemirah Kamanya  1 , Kara Chris Bhatt  1 , Andrew Braham  1 , Miranda Kubek  1 , Summer Hawthorne  1 , Gonzalo Campillo-Alvarado  1 , Avik Bhattacharjee  2 , Miriam A Bowring  1 , Robert V O'Brien  1
Affiliations

Chemodivergent synthesis of cis-4-hydroxyprolines from diastereomerically enriched epoxides

Clement DaSilva et al. Org Biomol Chem. .

Abstract

A method for synthesis of cis-4-hydroxyproline analogs is described. A cis epoxide is converted into a cis-4-hydroxyproline, while the trans epoxide is converted into a ketone or α-aminolactone in the presence of Lewis and Brønsted acids. We propose the divergent chemoselectivity is controlled by H-bonding within the cis epoxide.

PubMed Disclaimer

LinkOut - more resources